2-[(E)-3-phenyl-2-propenyl]cyclohexanone | 84624-35-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[(E)-3-phenyl-2-propenyl]cyclohexanone
• 英文别名: (E)-2-cinnamylcyclohexanone；2-(cinammyl)-cyclohexanone；2-cinnamylcyclohexanone；(+/-)-2-trans-cinnamyl-cyclohexanone；(+/-)-2-trans-Cinnamyl-cyclohexanon；2-[(E)-3-phenylprop-2-enyl]cyclohexan-1-one
• CAS: 84624-35-1
• 化学式: C₁₅H₁₈O
• 分子量: 214.307
• InChiKey: FSTALRCSLSFKOP-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-[(E)-3-phenyl-2-propenyl]cyclohexanone 在 正丁基锂 、 sodium acetate 、 二异丙胺 作用下， 以 乙醇 为溶剂， 反应 0.75h， 生成 3-Dimethoxymethyl-2-(4-fluoro-phenyl)-7-((E)-3-phenyl-allyl)-4,5,6,7-tetrahydro-2H-indazole
  参考文献：
  名称：

  HMG-CoA reductase inhibitors: design, synthesis, and biological activity of tetrahydroindazole-substituted 3,5-dihydroxy-6-heptenoic acid sodium salts

  摘要：

  Compounds comprising a series of 7-[2-(4-fluorophenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-3,5-dihydroxy-6-heptenoic acid sodium salts (18) were synthesized and tested for their ability to inhibit HMG-CoA reductase in a partially purified enzyme preparation and cholesterol biosynthesis from acetate in cultured HEP-G2 cells. Changing the size of the saturated ring of the tetrahydroindazole nucleus did not improve potency, but incorporation of substituents at the 7-position resulted in up to 1700-fold improvement in inhibitory potency. Structure-activity studies revealed that the most potent compounds possess a substituted benzyl group at the 7-position, with a preference for steric bulk at the para position of the benzene ring. The most potent enzyme inhibitor (18t, IC50 = 3.0 nM) is approximately 3-fold more potent than lovastatin sodium salt (2). The most potent cholesterol biosynthesis inhibitor in HEP-G2 cells (18q, IC50 = 0.078 muM) is slightly less potent than 2 (sodium salt). Molecular modeling studies suggested that, when compared to the parent compound (18b) lacking the appropriate 7-substituent, 18t overlaps better with 2 and literature inhibitors 5 and 6 in a hydrophobic binding region adjacent to the enzyme active site.

  DOI：

  10.1021/jm00075a024
• 作为产物：
  描述：

  diethyl (2-oxocyclohexyl)phosphonate 在 lithium aluminium tetrahydride 、 sodium hydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.5h， 生成 2-[(E)-3-phenyl-2-propenyl]cyclohexanone
  参考文献：
  名称：

  用的LiAlHα-完全取代的β酮膦酸酯的Dephosphonylation 4 ; 使用膦酸酯作为临时活化基团的酮的区域选择性烷基化

  摘要：

  β-酮膦酸酯的烷基化是通过用n -BuLi乳化β-酮膦酸酯，然后添加烷基卤来进行的。通过用LiAlH 4处理烯醇锂，然后用H 2 SO 4水溶液淬灭，将获得的α-完全取代的β-酮膦酸酯脱膦酰化。整个过程代表了酮区域选择性烷基化的新途径。

  DOI：

  10.1016/s0040-4039(97)00975-1

文献信息

• Palladium-Catalyzed Allylic Alkylation of Simple Ketones with Allylic Alcohols and Its Mechanistic Study
  作者：Xiaohong Huo、Guoqiang Yang、Delong Liu、Yangang Liu、Ilya D. Gridnev、Wanbin Zhang

  DOI：10.1002/anie.201403410

  日期：2014.6.23

  Allylic alcohols were directly used in Pd‐catalyzed allylic alkylations of simple ketones under mild reaction conditions. The reaction proceeded smoothly at 20 °C by the concerted action of a Pd catalyst, a pyrrolidine co‐catalyst, and a hydrogen‐bonding solvent, and does not require any additional reagents. A computational study suggested that methanol plays a crucial role in the formation of the

  在温和的反应条件下，烯丙醇直接用于钯催化的简单酮的烯丙基烷基化反应。在20°C下，Pd催化剂，吡咯烷助催化剂和氢键合溶剂的协同作用使反应顺利进行，不需要任何其他试剂。一项计算研究表明，甲醇通过降低活化势垒在π-烯丙基铝配合物的形成中起着至关重要的作用。
• Highly Controlled Chemoselectivity of Tin Enolate by Its Hybridization State. Anionic Complex of Tin Enolate Coordinated by Tetrabutylammonium Bromide as Halo Selective Reagent
  作者：Makoto Yasuda、Keiko Hayashi、Yasuhiro Katoh、Ikuya Shibata、Akio Baba

  DOI：10.1021/ja972190s

  日期：1998.2.1

  bromide (Bu4NBr) to neutral four-coordinated tin(IV) enolates 1(e). The highly coordinated enolates which attained a marked change in chemoselectivity have higher nucleophilicity to organic halides. In addition, they showed low nucleophilicity toward carbonyl moieties by the coordination of the bromide anion, whereas carbonyl addition readily proceeds using the usual four-coordinated tin enolate. NMR studies

  有机锡 (IV) 烯醇化物的反应性和/或选择性的控制已通过有效改变锡的杂化状态的高配位方法进行了研究。阴离子锡络合物，五配位锡烯醇化物 1(h)，是通过溴化物阴离子从四丁基溴化铵 (Bu4NBr) 与中性四配位锡 (IV) 烯醇化物 1(e) 配位形成的。化学选择性发生显着变化的高度配位的烯醇化物对有机卤化物具有更高的亲核性。此外，它们通过溴化物阴离子的配位对羰基部分显示出低亲核性，而使用通常的四配位锡烯醇盐很容易进行羰基加成。核磁共振研究揭示了 HMPA 或溴化物阴离子配位锡烯醇化物在四配位烯醇化物 1c(e) 和五配位烯醇化物 1c(h) 之间的平衡中的生成，显示出相当大的高场位移 δ(119Sn) 和增加的值耦合常数 1J(119Sn-13C)。在详细...
• Alkylation via tris(dialkylamino)sulfonium enolates
  作者：R. Noyori、I. Nishida、J. Sakata

  DOI：10.1016/s0040-4039(00)71493-6

  日期：1980.1

  Tris(dialkylamino)sulfonium enolates generated from tris(diethylamino)sulfonium difluorotrimethylsiliconate and enol silyl ethers are readily alkylated by various alkyl halides under mild conditions.

  由三氟二甲基三甲基硅酸三（二乙基氨基）ulf和烯醇甲硅烷基醚生成的三（二烷基氨基）ulf烯醇盐很容易在温和的条件下被各种烷基卤化物烷基化。
• Boron trifluoride-catalyzed reaction of alkyl fluoride with silyl enolate, allylsilane, and hydrosilane
  作者：Koji Hirano、Kazuya Fujita、Hideki Yorimitsu、Hiroshi Shinokubo、Koichiro Oshima

  DOI：10.1016/j.tetlet.2004.01.145

  日期：2004.3

  Alkylation of silyl enolates with tert-alkyl or allylic fluorides proceeds smoothly in the presence of a catalytic amount of boron trifluoride to afford the corresponding carbonyl compounds. Allylation and reduction of alkyl fluorides with allylsilane and hydrosilane, respectively, occur under BF3 catalysis.

  在催化量的三氟化硼的存在下，用叔烷基或烯丙基氟化物进行烯基甲酸酯的烷基化反应进行得很顺利，从而得到相应的羰基化合物。在BF 3催化下，烷基氟与烯丙基硅烷和氢硅烷的烷基化和还原反应分别发生。
• Kinetics and Mechanisms of the Reactions of π-Allylpalladium Complexes with Nucleophiles
  作者：Oliver Kuhn、Herbert Mayr

  DOI：10.1002/(sici)1521-3773(19990201)38:3<343::aid-anie343>3.0.co;2-x

  日期：1999.2.1

  Which nucleophiles are capable of attacking the allyl ligand of the Pd-stabilized allyl cation 1? This question is answered by the electrophilicity parameter of 1 which is derived from kinetic investigations.

  哪些亲核试剂能够攻击Pd稳定的烯丙基阳离子1的烯丙基配体？这个问题是由动力学研究得出的亲电性参数1回答的。